52776-45-1

Usage

Uses

Used in Pharmaceutical Industry:
2,2-Dimethoxyadamantane is used as a pharmaceutical agent for its potential anti-inflammatory and antiviral properties, offering therapeutic benefits in the treatment of various conditions.
Used in Organic Synthesis:
2,2-Dimethoxyadamantane is used as a building block in organic synthesis for creating more complex molecules, leveraging its unique molecular structure to facilitate the development of new compounds with specific functionalities.
Used in Lubricant Industry:
2,2-Dimethoxyadamantane is used as a lubricant additive due to its unique molecular structure and properties, which may enhance the performance characteristics of lubricants in various applications.

Upstream product

• 67-56-1 methanol 
• 97129-83-4 adamantanone N^β-[2'-(methylthio)adamantyl(2')-thio]-methylenehydrazone 
• 700-58-3 2-Adamantanone 
• 64-17-5 ethanol 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 700-58-3 2-Adamantanone 
• 675957-36-5 (R)-4-[(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane 
• 1310563-00-8 [2-(spiro[adamantan-2,2'-[1,3]dioxan]-4'-yl)ethyl] p-toluenesulfonate 

Relevant academic research and scientific papers

Observation of a stable carbocation in a consecutive Criegee rearrangement with trifluoroperacetic acid

Selective oxidative cleavage - cyclization of adamantane through the bridge carbon was developed in trifluoroperacetic acid (TFPAA). The methyl group in the bridge position was found to be the substituent that directs consecutive oxygen insertion into the cage structure during the course of a Criegee rearrangement. The formation of stable 5-methyl-4,6-dioxabishomoadamant-5-yl cation at -25°C was observed. Stable carboxonium ion formation allows control of the selectivity of further transformations. Hydrolysis leads to the stereospecific formation of endo, endo-3-hydroxy-7-acetoxybicyclo[3.3.1]nonane. Its single-crystal X-ray structure was obtained. An increase in temperature results in deprotonation of the 5-methyl-4,6-dioxabishomoadamant-5-yl cation to endo-3-trifluoroacetoxybicyclo[3.3.1]non-6-ene, which undergoes further epoxidation with TFPAA and acidic transannular cyclization in trifluoroacetic acid (TFAA). The described reactions can be used as a convenient method for the synthesis of bicyclo[3.3.1]nonane and oxaadamantane derivatives. The proposed mechanism for each transformation, as well as supporting ab initio theoretical calculations of the strain energy and the stabilization energy of the relevant oxacage structures, are discussed.

Synthesis of Functionalized Aliphatic Acid Esters via the Generation of Alkyl Radicals from Silylperoxyacetals

We describe a catalytic method for the synthesis of a variety of functionalized aliphatic acid esters using silylperoxyacetals, which are versatile alkyl radical precursors with a terminal ester moiety. In the presence of an appropriate transition-metal catalyst, the in situ generation of alkyl radicals and the subsequent bond-forming process proceeds smoothly to afford synthetically valuable aliphatic acid derivatives. The present method can be applied to the efficient synthesis of a pharmaceutically important 1,1-diarylalkane motif. In addition, a novel strategy for the synthesis of structurally diverse hydroxy acid derivatives via a C?O bond formation process that utilizes TEMPO has been developed.

Synthesis of 4-(aminoalkyl) substituted 1,3-dioxanes as potent NMDA and σ receptor antagonists

Elongation of the distance between the oxygen heterocycle and the basic amino moiety or ring expansion of the oxygen heterocycle of the NMDA receptor antagonists dexoxadrol and etoxadrol led to compounds with promising NMDA receptor affinity. Herein the c

Photochemical acetalization of carbonyl compounds in protic media using an in situ generated photocatalyst

Carbonyl compounds are conveniently converted into their corresponding dimethyl acetals in good yields and short reaction times by means of a photochemical reaction in methanol with a catalytic amount of chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone, CA) as the sensitizer. Using aldehydes gives better results than using ketones, which also tend to form enol ethers as side products. These results are similar to those of simple acid-catalyzed acetalization reactions, suggesting the involvement of a photochemically generated acid. On the basis of steady state and laser flash photolysis data the reaction is proposed to involve the in situ generation of a photocatalyst (2,3,5,6-tetrachloro-1,4-hydroquinone, TCHQ) via reaction of CA with the solvent. The acetalization process is initiated by ionization of TCHQ, followed by loss of a proton to the solvent or the carbonyl, which starts a catalytic reaction. The photocatalyst is regenerated via a disproportionation reaction.

Acid-base reactions of adamantanethione S-methylide and its spiro-1,3,4-thiadiazoline precursor

The spiro-1,3,4-thiadiazoline 1 loses N2 at 45°C, and, as recently reported, the short-lived adamantanethione S-methylide (2) is an active 1,3-dipole. Interception of 2 by acids HX consists of CH2-protonation and ion recombination. Even 1 acts as HX vs 2 and - after electrocyclic ring opening of the anion (13 →15) - affords the dithioacetal C22H32N2S2 (14). The Δ3-thiadiazoline 1 is converted by base or acid catalysis to the Δ2-tautomer 21. Amidrazones (25, 26) are formed from 1 and sec-amines. The mechanisms are discussed and the structures elucidated.

Photochemical Behaviour of 4-Methylene-2-adamantanone, an Exocyclic β,γ-Unsaturated Ketone

The photochemistry of 4-methylene-2-adamantanone (1) was studied in different solvents and under direct and sensitized irradiation.Depending on the conditions, β,g-unsaturated ketone 1 underwent reactions characteristic of isolated ketones or alkenes.Direct irradiation of 1 in benzene afforded a mixture of 2-methylenenoradamantane (11) and 4-methylenebicyclonon-2-en-7-carbaldehyde (12).Irradiation of 1 in benzene in the presence of benzophenone gave oxetanes 10, while the major products in acetone sensitized photolysis were identified as syn- and anti-4-(3-oxobutyl)-2-adamantanones (8).In protic solvent (ethanol), 1 reacted smoothly to give ketal 13.The photochemical reactions that proceeded through intramolecular interactions were not observed.

ACID-BASE REACTIONS OF 1,3,4-THIADIAZOLINES AND THIOCARBONYL YLIDES; 1,3,4-THIADIAZOLINE-2-SPIRO-2'-ADAMANTANE

The surprising formation of C22H32N2S2 from the title compound 1 at 45 oC involves the interaction of the basic adamantanethione S-methylide (2) with its acidic precursor 1, in the course of which the anion 6 undergoes electrocyclic ring opening; the acid and base functions offer the clue to a prolific chemistry of the thiadiazoline 1 and the thiocarbonyl ylide 2.